Nu-(3,4-dichlorobenzyl)-nu-(n-dodecyl)-nu,nu-di-(2-hydroxyethyl) ammonium chloride and preparation thereof



Patented June 15, 1954 N (3,4-DICHLOROBENZYL) -N- (ll-DODECYL) N,N DI(2-HYDROXYETHYL)AMM ONIUM CHLORIDE AND PREPARATION THEREOF Louis L.Hallock, Terre Haute, Ind., assignor to Sterling Drug Inc., New York, N.Y., a corporation of Delaware No Drawing. Application June 2, 1952,Serial No. 291,298

Advantageously, this reaction is carried out by heating approximatelyequi-molecular proportions of the two reactants together at 40100 C. Ifdesired, the condensation product thus obtained can be submitted topurification procedures.

My invention is illustrated by the following example without, however,being limited thereto.

Example A mixture of 55 g. of N-(n-dodecyl) diethanolamine and 39.1 g.of 3,4-dichlorobenzy1 chloride was heated under reflux for about twelvehours. The thick colorless reaction product thus obtained was dissolvedin ethanol, the solution was filtered, and the ethanol was then removedfrom the solution by distillation. The residue thus obtained wasrecrystallized from acetone and dried at 50 C. at 1 mm. to yield 55 g.of N-(3,4-dichlorobenzyl) -N-(n-dodecyl) -N,N-di (2 hydroxyethyhammoniumchloride which melted at 95.0- 96.5 C. This product was a veryhygroscopic, colorless powder which was soluble in water to the extentof 10% (weight/volume). A 1% solution of the compound had pH 7.2.

N (3,4-dich1oroloenzy1) -N (n-d0decy1-N,N di- (Z-hydroxyethyl) ammoniumchloride was found to have high activity against many species ofbacteria, for example Staphylococcus aureus, Clostridium welchz'i,Mycobacterium tuberculosis, Streptococcus pyogenes, Shigclladysentefiae, Pasteurella pestis, Eberthella typhi, and Streptococcusfaecalis, and fungi, for example, Trichophyton interdigitalc,Trichophyton mentagrophytes, Trz'chophyton yyi seum, and Mom'lia aZ-bicans.

Iclaim:

1. N -(3,4-dich1orobenzyl) -N- (n-dodecyl) -N,N- di-(Z-hydroxyethyl)ammonium chloride, having 2. The process which comprises interacting N-(n dodecyl) diethanolamine with 3,4 dichlorobenzyl chloride.

References Cited in the file of this patent UNITED STATES PATENTS NumberName Date 1,883,042 Somerville Oct. 1.8, 1932 2,003,960 Tonkin et a1June 4, 1935 2,214,352 Schoeller et al. Sept. 10, 1940 2,302,805Schussler Nov. 24, 1942 FOREIGN PATENTS Number Country Date 458,033Great Britain Dec. 8, 1936

1. N-(3,4-DICHLOROBENZYL) -N-(N-DODECYL)-N,NDI-(2-HYDROXYETHYL) AMMONIUMCHLORIDE, HAVING THE FORMULA